Methyl 4-bromo-3-methoxy-2-methylbenzoate → Benzoic acid, 4-cyano-3-methoxy-2-methyl-, methyl ester

Participants

Reaction Conditions

Reaction Steps

To a sealed tube vessel was added methyl 4-bromo-2-methyl-3-(methyloxy)benzoate (280 mg, 1.08 mmol), copper (I) cyanide (97 mg, 1.08 mmol) and dimethylformamide (2 mL). The mixture was heated at 150° C. for 24 hours, then was cooled to room temperature and filtered through a pad of Celite. After washing the Celite with ethyl acetate, the combined filtrate was washed with 5% aqueous lithium chloride, and brine, then dried over anhydrous sodium sulfate. Filtration and concentration afforded a brown residue that was purified by silica gel column chromatography. Eluting with 10% ethyl acetate in hexane, purified fractions were pooled and concentrated to afford 150 mg, 0.73 mmol (68%) of methyl 4-cyano-2-methyl-3-(methyloxy)benzoate. 1H NMR (400 MHz, CDCl3): 7.61 (d, 1H), 7.47 (d, 1H), 3.99 (s, 3H), 3.93 (s, 3H), 2.49 (s, 3H). MS (EI) for C11H11NO3: 206 (MH+).

Provenance & Evidence